Timothy Flindell Caffrey
Timothy Flindell Caffrey
Obituary
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Timothy Caffrey Obituary
Though he traveled the world, Tim's heart lived at home with his family and pets. He found joy in the simple pleasures: humming show tunes from Carousel to Sweeney Todd, walking his faithful yellow Lab, Wrigley, and honoring family traditions at the holidays. More than anything, Tim loved his family. Being a dad was the role he was proudest of, and he played it with a generous heart and unfailing humor. He took an active role in volunteering, reading to his daughters' school classes, coaching T-ball, and serving as president of the Beye School PTO.
Outgoing, upbeat, and compassionate, Tim possessed the uncanny ability to make any stranger a friend and created community wherever he went. He was a gifted storyteller, always keeping his audiences entertained by painting vivid pictures with his words and turning everyday encounters into hilarious, unforgettable memories. He had a song for every occasion and never failed to brighten any room he entered.
Tim is survived by his wife of 36 years, Kristin (née Bergsland), his daughters Katie and Carrie, and his siblings George Caffrey (Jean), Betsy Caffrey, Tina Garland (David), Stephen Caffrey (Amanda Wyss), Kate Caffrey (Michael Reed), his sister-in-law Tricia Caffrey, in-laws Tom Bergsland, Erica Bergsland (Jack Goodnow), Emily Bergsland (Robert Warren), Peter Bergsland (Lauren), and numerous nieces and nephews. He was preceded in death by his parents, his brother Jim, and his son Christopher.
A visitation will be held on Friday, August 15, 2025, from 5-8 pm at the Oak Park Conservatory (615 Garfield St., Oak Park, IL) in the Rubenstein Room. A celebration of Tim's life will be held at a future date.
In lieu of flowers, donations may be made to the CAST theatre program (https://www.castatjulian.org/donate) or the American Lung Association (https://action.lung.org).
To plant trees in memory, please visit the Sympathy Store.
20 Entries
Tim Montgomery
Earlier today
I have worked with Tim for over a decade with a number of clients and would always look for opportunities to partner with him because of how awesome he was to work with and what a fantastic facilitator Tim was!!! He was such an amazing professional at everything he did, but he always brought more than just his teaching and business skills to our clients because of his ability to connect with you personally. He spoke lovingly of his family. My thoughts and prayers are with you all at this time!!!
Joan M Dasher
Yesterday
I met Tim almost 20 years ago when I was a BlessingWhite newbie. He took me under his wing, so to speak, and trained me to facilitate several courses. He was a joy to work with -- so kind, empathetic, caring, funny and encouraging. I learned so much from Tim. Through the years, every conversation we had started with our families -- his love for his family shone through his happy smile as he talked. Tim is the kind of person that comes along rarely; I am so blessed to have known him. Thank you for sharing him with us!
Leah Clark
August 6, 2025
Tim was always a regular on the webinars I delivered. Seeing his name in the chat and reading the ridiculously kind comments he would make always put me at ease. His brand of personal generosity is very rare and I was lucky to know him even the littlest bit. My thoughts are with you, his family, at this sad time.
Deb Berman
August 6, 2025
Tim's humor, joy, kindness, and selflessness surrounded everything he did. As others have said here, a day at work with him was always a Great Day at Work. To Tim's beloved family and friends - I hold you in my heart and wish for you comfort and peace.
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Tom Kristoph
August 5, 2025
Working with Tim was never work. He brought out the best in all of us. We all learned something new from him whenever we were together.
Robert Anderson
August 5, 2025
Best work colleague ever! It was so much fun working with Tim. At The Executive Technique in 1986, he kept us laughing even during difficult times. He was warm and enthusiastic - an entertainer - and the ring leader of our work team. My sincerest condolences to his family.
Stace Williams
August 5, 2025
Tim was one of my favorite people at BlessingWhite. We shared so many experiences, work and social. All were memorable, and he made every one better.
One historical gem for me was the "rivalry" with a colleague about who was funnier. In the end, I thought of Tim as The Funny One.
My sincerest condolences to his beloved family and friends. May the memories of good times give you moments of piece, and may you laugh, really laugh, at every opportunity in honor of Tim's example.
Barbara Pelly
August 5, 2025
Tim was an amazing colleague and friend. Working with him and the partnership was special. Always willing to support not just his colleagues but the learners he taught was amazing. He has touched so many lives and he will be missed.
Annie McManus
August 5, 2025
I had the great opportunity to work with Tim. Though our paths didn't cross regularly, it was always a great day when I did have the chance to learn from him. He was a great colleague, facilitator, coach, and always brought humor, warmth, and kindness to every interaction. He will be missed so very much.
Janet FitzGerald
August 5, 2025
I am so sad to hear of Tim´s passing....a HUGE loss to all! He was the funniest character anyone ever got to know, and kept our team at work in stitches with his stories and movies he made with his good friend, Mark for our Christmas parties...so original and creative, and with such a big heart too. My heart goes out to all in his family!
Mary Ann Masarech
August 5, 2025
What a gift it was to work on projects with Tim. The world is a better place because he was born.
Diane DiResta
August 5, 2025
I will always remember Tim for his humor, creativity. and kindness. We had a fun time working at The Executive Technique. He lit up every room he entered. Sending my deepest condolences.
Maxime Patte
August 5, 2025
Il était un homme généreux et intelligent. Il restera pour moi « mister cosmopolitan », qu´est ce que nous avions rigolé avec cela ! Toutes mes pensées vont à toi Katie, à ta maman et à ta soeur. Je garde en mémoire le « au revoir » touchant et émouvant qu´il m´avait fait au départ de l´aéroport de Chicago en 2016 (la photo a été faite à ce moment-là). Bon vent Tim
Tanya Hubanks
August 4, 2025
To Katie: My thoughts are with you and your family. After meeting him at your MBA graduation, it was evident how proud he was of you and your accomplishments. Losing a parent to this heart-wrenching disease is so difficult. You will continue to make him proud as you excel in life. Sending you and your family my sincerest condolences. Warmly, Tanya
Brooke Trumm
August 4, 2025
All my love and deepest condolences to Carrie, Kristin, Katie, and the rest of their family.
Patrick Hoover
August 4, 2025
Tim was unique. He sure was at Aquinas when I knew him. I also thought of Tim as young, very young, forever young. And so I´m both saddened and surprised to learn of his passing. One of a kind, most definitely. As do so very many, I miss him.... Patrick J. Hoover
Jacques Fournier
August 4, 2025
Hi Katie, I never got to meet your dad but, as i was reading his obituary, i could tell what a loving dad he was and how hard it must be for you now. So i am sending you these few words of support from Chicago on behalf of your former colleagues at Lycee Francais. To your mom and to Carrie: my heartfelt condolences.
Jeanne Thomas Bunting
August 4, 2025
No words can express the shock of this news. We shared so many fun memories from high school. Tim was the leader of the pack.
Kristin, I can´t image your grief. You two were made for each other.
Sending love and support to you and your girls during this very difficult time.
Laurie Kattuah-Snyder
August 4, 2025
I´m deeply saddened to hear about Tim´s passing. I´ll always remember how freely he sang and joked, creating an atmosphere where everyone felt welcome to do the same. To Kristin, his daughters, and his siblings-I´m holding you in my thoughts and prayers, wishing you strength, peace, and healing during this incredibly difficult time.
Amy Melvin
August 4, 2025
Sending our sincerest condolences. Tim & family are the best alley neighbors. Leo is forever grateful for the fish tank Tim gifted him a few years ago. Tim´s cheerful greetings will be missed.
Sincerely,
The Malcolm-Melvin family
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